Ammonium formate → HCID 68671304, compound

HRID 1773380Notes

Reaction equation

HRID 1773380 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:53]=[C:54]([F:56])[CH:55]=1)[CH2:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([C:15]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[N:10]=[C:9]2[NH:34][C:35](=[O:52])[C:36]1[CH:41]=[CH:40][C:39]([N:42]2[CH2:47][CH2:46][N:45]([CH3:48])[CH2:44][CH2:43]2)=[CH:38][C:37]=1[N+:49]([O-])=O.C([O-])=O.[NH4+]>CO.[Pd]>[NH2:49][C:37]1[CH:38]=[C:39]([N:42]2[CH2:47][CH2:46][N:45]([CH3:48])[CH2:44][CH2:43]2)[CH:40]=[CH:41][C:36]=1[C:35]([NH:34][C:9]1[C:8]2[C:12](=[CH:13][CH:14]=[C:6]([CH2:5][C:4]3[CH:53]=[C:54]([F:56])[CH:55]=[C:2]([F:1])[CH:3]=3)[CH:7]=2)[N:11]([C:15]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:10]=1)=[O:52]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 68672067HCID 68672067, compound

Product 1

HCID 68671304HCID 68671304, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of N-[5-(3,5-difluoro-benzyl)-1-trityl-1H-indazol-3-yl]-4-(4-methyl-piperazin-1-yl)-2-nitro-benzamide (170 mg, 0.236 mmol), 10% Pd—C (10 mg) and ammonium formate (25 mg, 0.4 mmol) in methanol (5 mL) was stirred for 18 hours at room temperature. The catalyst was filtered off and the solution was concentrated. The residue was dissolved in dichloromethane, washed with aqueous solution of NaHCO3, dried and concentrated to yield title compound (145 mg, 87%).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe solution was concentrated
  3. dissolutionThe residue was dissolved in dichloromethane
  4. washwashed with aqueous solution of NaHCO3
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-72b63a637618467a9336f93d21e2065c
Source dataset
uspto-grants-2016_02
Patent number
US09255087B2

Reaction notes

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